Acetanilide Highly Selective Ch Bond Functionalization / Halogenation

The aromatic halide structures broadly exist in both natural products and synthetic drugs, and are also important motifs of many natural products and synthetic drugs. Aryl halides are broadly utilized to construct C-C, C-N, C-O bonds in organic synthetic chemistry via transition-metal-catalyzed coupling reactions.Many disadvantages, such as low selectivity, low yields, a certain extent of danger in the handling for the use of diazotization or alkyl lithium, etc, exist in the traditional methods for halogenating arenas.In this thesis, we developed a highly regioselective halogenation of acetanilide via palladium-catalyzed C-H bond functionalization. We chose Pd(OAc)₂,Cu(OAc)₂ as the catalyst system and CuX₂ as the halides sourse, and then got the halogenation results of a series of substituted compounds with the backbones of acetanilide in good yield and high selectivity.We did the pilot studies of the mechanism of the reaction, and we believe that the reaction may undergo a Pd(II)-Pd(IV) process and then produce the target halogenated products via reductive elimination.